Cosmetic compositions and an emulsion composition

ABSTRACT

A cosmetic composition and an emulsion composition respectively comprising 0.1 to 99 weight % of an oily component and 99.9 to 1 weight % of a watery component are are provided and the oily component in the compositions comprises 85 or more weight % of cis-Δ9-octadecenoic acid or derivatives thereof and contains 90 weight % or more of a cis-Δ9-alkenoic acid or derivatives thereof and 10 weight % or less of fatty acids other than the cis-Δ9-alkenoic acid, derivatives thereof or other oily components. The cosmetic composition showing superior feeling in use and superior storage stability than conventional products and the emulsion composition showing superior stability of emulsion than conventional products can be provided because the oily component contains cis-Δ9-octadecenoic acid or derivatives thereof in a high concentration.

This application is a divisional of Ser. No. 08/066,017, filed May 27,1993, now U.S. Pat. No. 5,589,515 which is a 35 U.S.C. §371 applicationof International Application Ser. No. PCT/JP92/01229, filed Sep. 25,1992.

TECHNICAL FIELD

The present invention relates to a cosmetic composition and an emulsioncomposition comprising cis-Δ9-octadecenoic acid or derivatives thereofin the oily component in a high concentration.

BACKGROUND ART

A cosmetic composition containing cis-Δ9-octadecenoic acid (oleic acid)or derivatives thereof in a high concentration has not been knownheretofore.

Conventional oleic acids and derivatives thereof have a bad smell, arecolored, cause skin irritation, have a poor feel in use and have poorstorage stability tending to further increase the poor smell and colordescribed above.

A method of production of a high purity oleic acid was disclosed inJapanese Patent Application Laid Open No. 1986-297 (Japanese PatentPublication No. 1990-57120). The following methods of production ofderivatives of the high purity oleic acid were also disclosed: a methodof production of glycerol monooleate in Japanese Patent Application LaidOpen No. 1987-132841, a method of production of propylene glycolmonooleate in Japanese Patent Application Laid Open No. 1987-138451, amethod of production of polyalkylene glycol monooleate in JapanesePatent Application Laid Open No. 1987-138452, a method of production ofsorbitan monooleate in Japanese Patent Application Laid Open No.1987-142141, a method of production of polyalkylene glycol alkyl etheroleate in Japanese Patent Application Laid Open No. 1987-153250, amethod of production of polyoxyalkylene polyalcohol oleate in JapanesePatent Application Laid Open No. 1987-153251, a method of production ofpolyoxyalkylene polyalcohol oleate in Japanese Patent Application LaidOpen No. 1987-153252, a method of production of oleic esters in JapanesePatent Application Laid Open No. 1987-153253, a method of production ofpolyalkylene glycol oleate in Japanese Patent Application Laid Open No.1987-153254, a method of production of polyoxyalkylene glycol monooleatein Japanese Patent Application Laid Open No. 1987-153255 and a method ofproduction of polyglycerol oleate in Japanese Patent Application LaidOpen No. 1987-153256. It has been suggested that these high purity oleicacids and derivatives thereof have no color, no smell, are stable, causelittle skin irritation and can be utilized in the field ofpharmaceuticals, cosmetics, foods, synthetic resins, lubricants,biochemicals and the like. However no description can be found onspecific cosmetic compositions.

The present invention has the object to provide a cosmetic compositionand an emulsion composition both comprising cis-Δ9-octadecenoic acid orderivatives thereof in a high concentration and to provide a cosmeticcomposition having superior feeling in use and superior storagestability than conventional products and an emulsion composition showingsuperior emulsion stability than conventional products.

DISCLOSURE OF THE INVENTION

The present invention provides a cosmetic composition which comprises0.1 to 99 weight % of an oily component and 99.9 to 1 weight % of awatery component, the oily component comprising 85 or more weight % ofcis-Δ9-octadecenoic acid or derivatives thereof and containing 90 weight% or more of a cis-Δ9-alkenoic acid or derivatives thereof and 10 weight% or less of fatty acids other than the cis-Δ9-alkenoic acid,derivatives thereof or other oily components.

The present invention also provides an emulsion composition whichcomprises 0.1 to 99 weight % of an oily component and 99.9 to 1 weight %of a watery component, the oily component, comprising 85 or more weight% of cis-Δ9-octadecenoic acid or derivatives thereof, containing 90weight % or more of a cis-Δ9-alkenoic acid or derivatives thereof and 10weight % or less of fatty acids other than the cis-Δ9alkenoic acid,derivatives thereof or other oily components and having an oilysubstance insoluble in the watery component and a surfactant which isdissolved or emulsified in the watery component.

THE MOST PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION

The invention is described in more detail in the following.

The ratio of the oily component and the watery component is 0.1 to 99weight %: 99.9 to 1 weight %. However, this ratio is adopted for generalcosmetic compositions and the ratio is different depending on the kindof the cosmetic composition. For example, the following ratios can beadopted: for skin lotion, 0.5 to 20 weight %: 99.5 to 80 weight %; forskin cream, 10 to 85 weight %: 90 to 15 weight %; for milk lotion, 3 to50 weight %: 97 to 50 weight %; and for cleansing foam, 30 to 70 weight%: 70 to 30 weight %.

The cis-Δ9-alkenoic acid in the invention is a fatty acid having onecis-unsaturated bond at the 9-position, such as cis-Δ9-octadecenoic acid(generally called oleic acid), cis-Δ9-hexadecenoic acid (generallycalled palmitoleic acid) and the like.

The derivatives of the cis-Δ9-alkenoic acid (includingcis-Δ9-octadecenoic acid) comprise the following derivatives:

(1) Salts: salts of alkali metals, such as sodium, potassium and thelike; ammonium salts; morpholine salts; salts of alkylamines, such asmethylamine, ethylamine, butylamine and the like; salts ofalkanolamines, such as monoethanolamine, diethanolamine,triethanolamine, triisopropanolamine, 2-amino-2-methyl-1-propanol,2-amino-2-methyl-1,3-propanediol; salts of basic amino acids, such asarginine and the like; and the like salts;

(2) Amides (these amides are cis-Δ9-alkenoic acid amides): amides withalkylamines or alkenylamines, such as methylamine, ethylamine,butylamine, cis-Δ9-alkenyl amines and the like; amides withalkanolamines, such as monoethanolamine, diethanolamine,isopropanolamine, 2-amino-2-methyl-1-propanol,2-amino-2-methyl-1,3-propanediol and the like; polyoxyethylatedcompounds and polyoxypropylated compounds of these amides; amides andsalts of amides of amino acids, such as glutamic acid and the like;amides with sodium N-methyltaurine; cis-Δ9-alkenoyl peptides, such ascis-Δ9-alkenoyl collagen and the like; and the like amides;

(3) Esters: esters with monohydric alcohols, such as methanol, ethanol,propanol, isopropanol, butanol, neopentanol, hexanol, octanol,2-ethylhexanol, nonanol, isononanol, decanol, dodecanol, isotridecanol,tetradecanol, hexadecanol, isohexadecanol, hexyldecanol, octadecanol,isooctadecanol, eicosanol, 2-octyldodecanol, docosanol, octacosanol,triacontanol, aryl alcohol, hexadecenol, cis-Δ9-octadecenol, decocenol,cyclohexanol, lanolin alcohol, terpene alcohol, benzyl alcohol and thelike, and esters with polyoxyethylated compounds or polyoxypropylatedcompounds of the monohydric alcohols; esters with polyhydric alcohols,such as ethylene glycol, propylene glycol, butylene glycol, glycerol,polyglycerols, trimethylolpropane, pentaerythritol, sorbitol, mannitol,sorbitan and the like, and esters with polyoxyethylated compounds orpolyoxypropylated compounds of the polyhydric alcohols; esters withsugars, such as glucose, sucrose and the like; esters with sterols, suchas cholesterol, cholestanol, sitosterol and the like; esters and saltswith other hydroxyl compounds, such as tocopherol, oryzanol, guaiacol,gossypol, terpene alcohols, fluoroalcohols, isethionic acid and thelike; phospholipids in which the acyl group of a cis-Δ9-alkenoic acid isintroduced; and the like esters;

(4) Derivatives of cis-Δ9-alkenols: cis-Δ9-alkenols derived fromcis-Δ9-alkenoic acids; phosphoric esters, sulfuric esters,polyoxyethylated compounds, polyoxypropylated compounds,polyoxyethylated phosphoric esters, polyoxyethylated sulfuric esters,polyoxypropylated phosphoric esters and polyoxypropylated sulfuricesters of the cis-Δ9-alkenols and salts of these compounds; esters,partial esters and partial ester salts of cis-Δ9-alkenyl alcohols withsaturated, unsaturated, straight chain, branched chain, monovalent orpolyvalent carboxylic acids or hydroxylated carboxylic acids derivedfrom these carboxylic acid, such as ethanoic acid, butanoic acid,2-ethylhexanoic acid, dodecanoic acid, octadecanoic acid,cis-Δ9-octadecenoic acid, succinic acid, adipic acid, sebacic acid,maleic acid, oxalic acid, citric acid, malic acid and the like; ethersof cis-Δ9-alkenols with alcohols, sugars or hydroxyl compounds describedin (3) in the above; and the like compounds; and

(5) Derivatives of cis-Δ9-alkenylamines: salts of cis-Δ9-alkenylaminesderived from cis-Δ9-alkenoic acids with acids, such as hydrochloricacid, sulfuric acid, nitric acid, phosphoric acid, ethanoic acid and thelike; quaternary ammonium salts having a cis-Δ9-alkenyl group;quaternary ammonium betaine having a cis-Δ9-alkenyl group; and the likecompounds.

As shown in the above, the derivatives of cis-Δ9-alkenoic acid of theoily component of the invention is an oily substance insoluble in thewatery component or a surfactant which is dissolved or emulsified in thewatery component. Therefore, the cosmetic composition of the inventionincludes a composition having two separated layers composed of the oilysubstance and the watery component, a homogeneous composition composedof the surfactant and the watery component and a homogeneous transparentor turbid composition having the oily substance dissolved, emulsified ordispersed in the watery component by the effect of the surface activeagent.

Preferable examples of the derivatives of the cis-Δ9-alkenoic acids asthe oily substance are esters of cis-Δ9-octadecenoic acid with ethanol,isopropanol, cis-Δ9-hexadecenol, cis-Δ9-octadecenol, isooctadecanol,cholesterol and tocopherol; glycerol tri-cis-Δ9-octadecenoate;cis-Δ9-octadecenoic acid; cis-Δ9-octadecenol and the like. Preferableexamples of the derivatives of the cis-Δ9-alkenoic acids as thesurfactant are monoesters of cis-Δ9-octadecenoic acid and glycerol orpolyglycerol, sorbitan mono- or sesqui-cis-Δ9-octadecenoate,polyoxyethylated sorbitan mono-cis-Δ9-octadecenoate, polyoxyethylatedsorbitol tri- or tetra-cis-Δ9octadecenoate, polyoxyethylene glycolmono-cis-Δ9-octadecenoate and polyoxyethylated cis-Δ9-octadecenyl ether.The particularly preferable examples for both of the oily-substance andthe surfactant are esters of cis-Δ9-octadecenoic acid.

In the invention, cis-Δ9-alkenoic acid and the derivative thereof whichare the oily component insoluble in the watery component can besolubilized or emulsified in the watery component much more easily byusing the surfactant of the derivatives of cis-Δ9-alkenoic acid incomparison to using other surface active agents and the stability ismuch more excellent. The weight ratio of the oily substance and thesurfactant in this case is varied depending on the kinds and the ratioof the oily component and the surfactant, other additives and the like.The ratio is generally in the range of 99 to 1:1 to 99 and preferably inthe range of 97 to 3:3 to 97.

The oily component other than those described above are all kinds ofoily components other than the cis-Δ9-alkenoic acids and the derivativesthereof. Examples are natural and synthetic oily substances, such asfatty acids and derivatives thereof other than the cis-Δ9-alkenoicacids, paraffin, kerosene, squalane, plant oils, animal oils, lanoline,haze wax, hexadecanol, isooctadecanol, silicone oils,fluorohydrocarbons, polyoxypropylated ethers, cholesterol, tocopheroland the like; surface active agents derived from fatty acids other thanthe cis-Δ9alkenoic acids, such as dodecandiethanolamide and the like;other surface active agents like polyoxyethylated alkylphenyl ether; andthe like.

The watery component functions as the moisturizing agent and theexamples include water, of course, and compounds which can be mixed withwater in any ratio, such as alcohols like ethanol, isopropanol, ethyleneglycol, propylene glycol, 1,3-butylene glycol, polyethylene glycols,glycerol, sorbitol, polyglycerols, polyvinyl alcohols and the like;sugars like glucose, sucrose and the like; mucopolysaccharides likehyaluronic acid and the like; amino acids like glutamic acid and thelike; proteins like collagen and the like; and the like compounds.

When other cis-Δ9-alkenoic acids such as palmitoleic acid are presenttogether with cis-Δ9-octadecenoic acid, the other cis-Δ9-alkenoic acidsexhibit the same effect as that of cis-Δ9-octadecenoic acid. The oilycomponent contains 85 weight % or more of cis-Δ9-octadecenoic acid and90 weight % or more of the cis-Δ9-alkenoic acid, preferably 90 weight %or more of cis-Δ9-octadecenoic acid and 93 weight % or more of thecis-Δ9-alkenoic acid, more preferably 95 weight % or more ofcis-Δ9octadecenoic acid and 97 weight % or more of the cis-Δ9-alkenoicacid and most preferably 97 weight % or more of cis-Δ9-octadecenoic acidand 99 weight % or more of the cis-Δ9-alkenoic acid. When the content ofcis- Δ9-octadecenoic acid is less than 85 weight % or the content of thecis-Δ9alkenoic acid is less than 90 weight %, the feeling in use of thecosmetic composition is not satisfactory.

The cosmetic composition of the invention may comprise componentsgenerally added to cosmetic compositions, such as drugs like vitamins,antibiotics and the like, nutrients, ultraviolet ray absorbents, carbonblack, titanium oxide, iron oxide, metallic soaps, calcium carbonate,silica, talc, colors, perfumes and the like, in addition to the oilycomponent and the watery component described above.

The cosmetic composition of the invention takes the form of liquid,cream, gel or solid depending on the mixed composition. It is used asskin lotion, cosmetic oil, milk lotion, lipstick, hair liquid, haircream, hair growth agent, foundation, various kinds of cream and thelike.

The emulsion composition of the invention may comprise various kinds ofadditives generally added to emulsion compositions.

The method of preparation of the cosmetic composition and the emulsioncomposition of the invention can be performed by compounding thecomponents described above. The order of the addition of the componentsis not particularly limited and components can be suitably selected andadded. The compounded components are suitably mixed by using variouskinds of mixer, various kinds of dispersing machine, various kinds ofemulsifying machine or the like to prepare the cosmetic composition andthe emulsion composition of the invention.

The reason that the stability of the product in the invention is veryexcellent when the derivative of cis-Δ9-octadecenoic acid is used as thesurfactant to emulsify or solubilize in the watery componentcis-Δ9-octadecenoic acid or the derivative which is insoluble in thewatery component can be considered as following: when the concentrationof cis- Δ9-octadecenoic acid or the derivative is high, mutualorientation and cohesion of the cis-Δ9-octadecenoyl group or thecis-Δ9-octadecenyl group in the molecule is considered to be enhancedand the molecular structure proper to the molecule is efficientlyexhibited; this is considered to have the effect on the better feelingin use of the cosmetic composition comprising cis-Δ9-octadecenoic acidor the derivative in a high concentration.

The cosmetic composition of the invention comprising cis-Δ9-octadecenoicacid or the derivatives thereof in the oily component in a highconcentration provides very excellent feeling in use and the result isremarkably superior than the cosmetic compositions comprisingcis-Δ9-octadecenoic acid or the derivatives thereof in a lowconcentration.

Cosmetic compositions prepared by using commercial oleic acid orderivatives thereof having low concentrations of cis-Δ9-octadecenoicacid as the material are colored or generate smell with passage of time.The cosmetic composition of the invention does not have such drawback.

The emulsion composition of the invention comprising cis-Δ9-octadecenoicacid or the derivative thereof in the oily component in a highconcentration has a very excellent stability of the emulsion.

EXAMPLE

The invention is described with reference to examples. However, theinvention is by no means limited by the examples.

In the Examples and Comparative Examples, oleic acid or oleic acidderivatives containing various kinds of cis-Δ9-octadecenoic acid andderivatives thereof were used as the oily component. The concentrationwas represented by the purity of cis-Δ9-octadecenoic acid or acis-Δ9-alkenoic acid in the oleic acid.

When the concentration of cis-Δ9-octadecenoic acid or its derivative isvaried in a composition using two or more kinds of oleic acid or oleicacid derivatives, the oleic acids or the oleic acid derivatives havingthe same purity of the cis-Δ9-octadecenoic acid were used forcompounding in the composition.

In the Examples and Comparative Examples, "%" means "weight %". Theoleic acid or the oleic acid derivative containing 57% ofcis-Δ9-octadecenoic acid and 66 weight % of cis-Δ9-alkenoic acid used inComparative Examples is a commercial oleic acid or a derivative from thecommercial oleic acid.

Method of evaluation of the cosmetic composition, method of evaluationof storage stability of an emulsion composition and method of analysisof purity of a cis-Δ9-alkenoic acid containing cis-Δ9-octadecenoic acidare described in the following.

Method of evaluation of the feeling in use

Overall feeling in use including all of smell, extension, refreshingfeeling and emollient effect was evaluated by 20 women panellers and theresult is shown by the number of the panellers whose answer was good.

Method of evaluation of storage stability of an emulsion composition

An oily component (including oily substances and surfactants) and awatery component were mixed by shaking mildly and then emulsified byusing a homogenizer (DX-3 type, a product of Nippon Seiki SeisakushoCo., Ltd.) at 10,000 rpm for 15 minutes. Condition of the emulsion wasevaluated by visual observation according to the following criterion:

stable: emulsified in a stable condition

slightly separated: slightly separated

separated: completely separated into two phases

Method of analysis of purity

Analysis was conducted by using an apparatus for gas chromatography(GC-9A, a product of Shimazu Seisakusho Co., Ltd.) equipped withcapillary columns which can separate isomers having different positionsof a double bond and different steric structures (SP-2560:0.25 mm×100 m,a product of Supelco Inc.).

Examples 1 to 5 and Comparative Examples 1 to 3

Skin lotions were prepared by using N-oleoyl-L-glutamic acids which areoleic acid derivatives having different purities shown in Table 1 as thesurfactant according to the formulation described below and the feelingin use was evaluated. The results are shown in Table 1.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily component                                                                surfactant: N-oleoyl-L-glutamic acid                                                                 3%                                                     watery components                                                             ethanol               10%                                                     purified water        85%                                                     sorbitol               2%                                                     ______________________________________                                    

                  TABLE 1                                                         ______________________________________                                                                     evaluation of                                    purity of cis-Δ9-                                                                        purity of cis-Δ9-                                                                   feeling in use                                   octadecenoic acid                                                                              alkenoic acid                                                                             (number of                                       (%)              (%)         persons)                                         ______________________________________                                        Example 1                                                                             99.9         100         19                                           Example 2                                                                             99           99.5        17                                           Example 3                                                                             95           97          15                                           Example 4                                                                             90           93          15                                           Example 5                                                                             85           90          13                                           Comparative                                                                           80           86          7                                            Example 1                                                                     Comparative                                                                           70           78          1                                            Example 2                                                                     Comparative                                                                           57           66          0                                            Example 3                                                                     ______________________________________                                    

Examples 6 to 10 and Comparative Examples 4 to 6

Cleansing creams were prepared by using monosodium N-oleoylglutamateswhich are oleic acid derivatives having different purities shown inTable 2 as the surfactant according to the formulation described belowand the feeling in use was evaluated. The results are shown in Table 2.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily component                                                                surfactant: monosodium N-oleoylglutamate                                                              45%                                                   watery components                                                             purified water          50%                                                   polyethylene glycol      5%                                                   ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                                                     evaluation of                                    purity of cis-Δ9-                                                                        purity of cis-Δ9-                                                                   feeling in use                                   octadecenoic acid                                                                              alkenoic acid                                                                             (number of                                       (%)              (%)         persons)                                         ______________________________________                                        Example 6                                                                             99.9         100         20                                           Example 7                                                                             99           99.5        18                                           Example 8                                                                             95           97          16                                           Example 9                                                                             90           93          15                                           Example 10                                                                            85           90          13                                           Comparative                                                                           80           86          10                                           Example 4                                                                     Comparative                                                                           70           78          7                                            Example 5                                                                     Comparative                                                                           57           66          0                                            Example 6                                                                     ______________________________________                                    

Examples 11 to 15 and Comparative Examples 7 to 9

Skin lotions were prepared by using glycerol monooleates which are oleicacid derivatives having different purities shown in Table 3 andpolyoxyethylated (25 mols) oleyl ethers which are oleic acid derivativeshaving the same purities as those of the corresponding glycerolmonooleates as the surfactants according to the formulation describedbelow and the feeling in use was evaluated. The results are shown inTable 3.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily component                                                                surfactants: glycerol monooleate                                                                     3%                                                     polyoxyethylated (25 mols) oleyl ether                                                               2%                                                     watery components                                                             ethanol                10%                                                    purified water         82%                                                    sorbitol               3%                                                     ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                                                     evaluation of                                    purity of cis-Δ9-                                                                        purity of cis-Δ9-                                                                   feeling in use                                   octadecenoic acid                                                                              alkenoic acid                                                                             (number of                                       (%)              (%)         persons)                                         ______________________________________                                        Example 11                                                                            99.9         100         20                                           Example 12                                                                            99           99.5        19                                           Example 13                                                                            95           97          18                                           Example 14                                                                            90           93          18                                           Example 15                                                                            85           90          15                                           Comparative                                                                           80           86          9                                            Example 7                                                                     Comparative                                                                           70           78          0                                            Example 8                                                                     Comparative                                                                           57           66          0                                            Example 9                                                                     ______________________________________                                    

Examples 16 to 20 and Comparative Examples 10 to 12

Skin lotions were prepared by using L-α-dioleoyl phosphatidyl cholineswhich are oleic acid derivatives having different purities shown inTable 4 and polyoxyethylated (20 mols) sorbitan monooleates which areoleic acid derivatives having the same purities as those of thecorresponding L-α-dioleoyl phosphatidyl cholines as the surfactantsaccording to the formulation described below and the feeling in use wasevaluated. The results are shown in Table 4.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily component                                                                surfactants: L-α-dioleoyl phosphatidyl choline                                                   2%                                                   polyoxyethylated (20 mols) sorbitan                                                                    1%                                                   monooleate                                                                    watery components                                                             ethanol                  15%                                                  purified water           80%                                                  propylene glycol         2%                                                   ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                                                     evaluation of                                    purity of cis-Δ9-                                                                        purity of cis-Δ9-                                                                   feeling in use                                   octadecenoic acid                                                                              alkenoic acid                                                                             (number of                                       (%)              (%)         persons)                                         ______________________________________                                        Example 16                                                                            99.9         100         20                                           Example 17                                                                            99           99.5        20                                           Example 18                                                                            95           97          18                                           Example 19                                                                            90           93          15                                           Example 20                                                                            85           90          13                                           Comparative                                                                           80           86          8                                            Example 10                                                                    Comparative                                                                           70           78          0                                            Example 11                                                                    Comparative                                                                           57           66          0                                            Example 12                                                                    ______________________________________                                    

Examples 21 to 25 and Comparative Examples 13 to 15

Skin lotions were prepared by using N-oleoyl-L-glutamic acids which areoleic acid derivatives having different purifies shown in Table 5 andhexaglycerol monooleates which are oleic acid derivatives having thesame purities as those of the corresponding N-oleoyl-L-glutamic acids asthe surfactants according to the formulation described below and thefeeling in use was evaluated. The results are shown in Table 5.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily component                                                                surfactants: N-oleoyl-L-glutamic acid                                                               2%                                                      hexaglycerol monooleate                                                                             3%                                                      watery components                                                             ethanol               10%                                                     purified water        85%                                                     ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                                                     evaluation of                                    purity of cis-Δ9-                                                                        purity of cis-Δ9-                                                                   feeling in use                                   octadecenoic acid                                                                              alkenoic acid                                                                             (number of                                       (%)              (%)         persons)                                         ______________________________________                                        Example 21                                                                            99.9         100         20                                           Example 22                                                                            99           99.5        19                                           Example 23                                                                            95           97          16                                           Example 24                                                                            90           93          14                                           Example 25                                                                            85           90          11                                           Comparative                                                                           80           86          3                                            Example 13                                                                    Comparative                                                                           70           78          0                                            Example 14                                                                    Comparative                                                                           57           66          0                                            Example 15                                                                    ______________________________________                                    

Examples 26 to 30 and Comparative Examples 16 to 18

Shaking lotions separated to two phases were prepared by usingisooctadecanyl oleates which are oleic acid derivatives having differentpurities shown in Table 6 as the oily substance and polyoxyethylated (20mols) sorbitan tetraoleates which are oleic acid derivatives having thesame purities as those of the corresponding isooctadecanyl oleates asthe surfactant according to the formulation described below and thefeeling in use was evaluated. The results are shown in Table 6.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance: isooctadecanyl oleate                                                                    8%                                                 surfactant: polyoxyethylated (20 mols) sorbitan                                                          0.2%                                               tetraoleate                                                                   watery components                                                             purified water             79.8%                                              ethanol                    10%                                                sorbitol                   1%                                                 glycerol                   1%                                                 ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                                                     evaluation of                                    purity of cis-Δ9-                                                                        purity of cis-Δ9-                                                                   feeling in use                                   octadecenoic acid                                                                              alkenoic acid                                                                             (number of                                       (%)              (%)         persons)                                         ______________________________________                                        Example 26                                                                            99.9         100         20                                           Example 27                                                                            99           99.5        20                                           Example 28                                                                            95           97          18                                           Example 29                                                                            90           93          17                                           Example 30                                                                            85           90          13                                           Comparative                                                                           80           86          4                                            Example 16                                                                    Comparative                                                                           70           78          0                                            Example 17                                                                    Comparative                                                                           57           66          0                                            Example 18                                                                    ______________________________________                                    

Examples 31 to 35 and Comparative Examples 19 to 21

Skin creams were prepared by using hexadecenyl oleates which are oleicacid derivatives having different purities shown in Table 7 as the oilysubstance and polyoxyethylated (10 mols) oleyl ethers which are oleicacid derivatives having the same purities as those of the correspondinghexadecenyl oleates as the surfactant according to the formulationdescribed below and the feeling in use was evaluated. The results areshown in Table 7.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance: hexadecenyl oleate                                                                     70%                                                  surfactant: polyoxyethylated (10 mols) oleyl ether                                                     5%                                                   watery components                                                             purified water           22%                                                  glycerol                 3%                                                   ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                                                     evaluation of                                    purity of cis-Δ9-                                                                        purity of cis-Δ9-                                                                   feeling in use                                   octadecenoic acid                                                                              alkenoic acid                                                                             (number of                                       (%)              (%)         persons)                                         ______________________________________                                        Example 31                                                                            99.9         100         20                                           Example 32                                                                            99           99.5        20                                           Example 33                                                                            95           97          19                                           Example 34                                                                            90           93          18                                           Example 35                                                                            85           90          13                                           Comparative                                                                           80           86          7                                            Example 19                                                                    Comparative                                                                           70           78          0                                            Example 20                                                                    Comparative                                                                           57           66          0                                            Example 21                                                                    ______________________________________                                    

Examples 36 to 40 and Comparative Examples 12 to 24

Skin creams were prepared by using ethyl oleates which are oleic acidderivatives having different purities shown in Table 8 as the oilysubstance and diglycerol monooleates which are oleic acid derivativeshaving the same purities as those of the corresponding ethyl oleates asthe surfactant according to the formulation described below and thefeeling in use was evaluated. The results are shown in Table 8.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance: ethyl oleate                                                                       65%                                                      surfactant: diglycerol monooleate                                                                  5%                                                       watery component                                                              purified water       30%                                                      ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                                                     evaluation of                                    purity of cis-Δ9-                                                                        purity of cis-Δ9-                                                                   feeling in use                                   octadecenoic acid                                                                              alkenoic acid                                                                             (number of                                       (%)              (%)         persons)                                         ______________________________________                                        Example 36                                                                            99.9         100         20                                           Example 37                                                                            99           99.5        20                                           Example 38                                                                            95           97          18                                           Example 39                                                                            90           93          18                                           Example 40                                                                            85           90          14                                           Comparative                                                                           80           86          7                                            Example 22                                                                    Comparative                                                                           70           78          1                                            Example 23                                                                    Comparative                                                                           57           66          0                                            Example 24                                                                    ______________________________________                                    

Examples 41 to 45 and Comparative Examples 25 to 27

Oleyl oleates of different purities were prepared by esterification ofoleic acids having different purities shown in Table 9 with oleylalcohols having the same purities as those of the corresponding oleicacids which were prepared by reduction of the oleic acids. Skin creamswere prepared by using the oleyl oleates as the oily substance andglycerol monooleates and sucrose monooleates which are oleic acidderivatives having the same purities as those of the corresponding oleyloleates, respectively, as the surfactants according to the formulationdescribed below and the feeling in use was evaluated. The results areshown in Table 9.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance: oleyl oleate                                                                           40%                                                  surfactants: glycerol monooleate                                                                       2.5%                                                 sucrose monooleate       1.5                                                  watery components                                                             purified water           53%                                                  propylene glycol         3%                                                   ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                                   purity of cis-                                                                         purity of cis-                                                                          evaluation of                                              Δ9-octa-                                                                         Δ9- feeling in use                                             decenoic acid                                                                          alkenoic acid                                                                           (number of                                                 (%)      (%)       persons)                                        ______________________________________                                        Example 41   99.9       100       20                                          Example 42   99         99.5      19                                          Example 43   95         97        18                                          Example 44   90         93        16                                          Example 45   85         90        13                                          Comparative Example 25                                                                     80         86         8                                          Comparative Example 26                                                                     70         78         0                                          Comparative Example 27                                                                     57         66         0                                          ______________________________________                                    

Examples 46 to 50 and Comparative Examples 28 to 30

Skin creams were prepared by using glycerol trioleates which are oleicacid derivatives having different purities shown in Table 10 as the oilysubstance and sorbitan sesquioleates and polyoxyethylated (20 mols)sorbitan monooleates which are oleic acid derivatives having the samepurities as those of the corresponding glycerol trioleates,respectively, as the surfactants according to the formulation describedbelow and the feeling in use was evaluated. The results are shown inTable 10.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance:                                                                           glycerol trioleate  75%                                           surfactants:                                                                              sorbitan sesquioleate                                                                               3.5%                                                    polyoxyethylated (20 mols) sorbitan                                                                 1.5%                                                    monooleate                                                        watery components:                                                                        purified water      17%                                                       sorbitol             3%                                           ______________________________________                                    

                  Table 10                                                        ______________________________________                                                   purity of cis-                                                                         purity of cis-                                                                          evaluation of                                              Δ9-octa-                                                                         Δ9- feeling in use                                             decenoic acid                                                                          alkenoic acid                                                                           (number of                                                 (%)      (%)       persons)                                        ______________________________________                                        Example 46   99.9       100       19                                          Example 47   99         99.5      19                                          Example 48   95         97        18                                          Example 49   90         93        15                                          Example 50   86         90        13                                          Comparative Example 28                                                                     80         86         7                                          Comparative Example 29                                                                     70         78         0                                          Comparative Example 30                                                                     57         66         0                                          ______________________________________                                    

Examples 51 to 55 and Comparative Examples 31 to 33

Skin creams were prepared by using 2-octyldodecyl oleates which areoleic acid derivatives having different purities shown in Table 11 asthe oily substance and pentaerythritol monooleates and polyoxyethylated(20 mols) oleyl ethers which are oleic acid derivatives having the samepurities as those of the corresponding 2-octyldodecyl oleates,respectively, as the surfactants according to the formulation describedbelow and the feeling in use was evaluated. The results are shown inTable 11.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance:                                                                           2-octyldodecyl oleate                                                                             20%                                           surfactants:                                                                              pentaerythritol monooleate                                                                         2%                                                       polyoxyethylated (20 mols) oleyl                                                                   1%                                                       ether                                                             watery components                                                                         purified water      72%                                                       glycerol             5%                                           ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                                   purity of cis-                                                                         purity of cis-                                                                          evaluation of                                              Δ9-octa-                                                                         Δ9- feeling in use                                             decenoic acid                                                                          alkenoic acid                                                                           (number of                                                 (%)      (%)       persons)                                        ______________________________________                                        Example 51   99.9       100       20                                          Example 52   99         99.5      19                                          Example 53   95         97        18                                          Example 54   90         93        18                                          Example 55   85         90        14                                          Comparative Example 31                                                                     80         86         9                                          Comparative Example 32                                                                     70         78         7                                          Comparative Example 33                                                                     57         66         0                                          ______________________________________                                    

Examples 56 to 60 and Comparative Examples 34 to 36

Milk lotions were prepared by using oleic acids having differentpurities shown in Table 12 and cholesterol oleates which are derivativesof these oleic acids as the oily substances and L-α-dioleoylphosphatidyl cholines which are oleic acid derivatives having the samepurities as those of the corresponding oleic acids as the surfactantaccording to the formulation described below and the feeling in use wasevaluated. The results are shown in Table 12.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substances:                                                                          oleic acid          2%                                                        cholesterol oleate  10                                            surfactant: L-α-dioleoyl phosphatidyl choline                                                           2%                                            watery component                                                                          purified water      86%                                           ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                                   purity of cis-                                                                         purity of cis-                                                                          evaluation of                                              Δ9-octa-                                                                         Δ9- feeling in use                                             decenoic acid                                                                          alkenoic acid                                                                           (number of                                                 (%)      (%)       persons)                                        ______________________________________                                        Example 56   99.9       100       20                                          Example 57   99         99.5      19                                          Example 58   95         97        18                                          Example 59   90         93        18                                          Example 60   85         90        15                                          Comparative Example 34                                                                     80         86        10                                          Comparative Example 35                                                                     70         78         7                                          Comparative Example 36                                                                     57         66         0                                          ______________________________________                                    

Examples 61 to 65 and Comparative Examples 37 to 39

Milk lotions were prepared by using glycerol dioleates which are oleicacid derivatives having different purities shown in Table 13 as the oilysubstance and L-arginine oleates which are oleic acid derivatives havingthe same purities as those of the corresponding glycerol dioleates asthe surfactant according to the formulation described below and thefeeling in use was evaluated. The results are shown in Table 13.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance:                                                                           glycerol dioleate   15%                                           surfactant: L-arginine oleate    1%                                           watery component                                                                          purified water      84%                                           ______________________________________                                    

                  TABLE 13                                                        ______________________________________                                                   purity of cis-                                                                         purity of cis-                                                                          evaluation of                                              Δ9-octa-                                                                         Δ9- feeling in use                                             decenoic acid                                                                          alkenoic acid                                                                           (number of                                                 (%)      (%)       persons)                                        ______________________________________                                        Example 61   99.9       100       20                                          Example 62   99         99.5      20                                          Example 63   95         97        18                                          Example 64   90         93        18                                          Example 65   85         90        18                                          Comparative Example 37                                                                     80         86        14                                          Comparative Example 38                                                                     70         78         9                                          Comparative Example 39                                                                     57         66         0                                          ______________________________________                                    

Examples 66 to 70 and Comparative Examples 40 to 42

Milk lotions were prepared by using tocopherol oleates which are oleicacid derivatives having different purities shown in Table 14 as the oilysubstance and sucrose monooleates which are oleic acid derivativeshaving the same purities as those of the corresponding tocopherololeates as the surfactant according to the formulation described belowand the feeling in use was evaluated. The results are shown in Table 14.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance:                                                                           tocopherol oleate   10%                                           surfactant: sucrose monooleate   3%                                           watery components                                                                         purified water      84%                                                       glycerol             3%                                           ______________________________________                                    

                  TABLE 14                                                        ______________________________________                                                   purity of cis-                                                                         purity of cis-                                                                          evaluation of                                              Δ9-octa-                                                                         Δ9- feeling in use                                             decenoic acid                                                                          alkenoic acid                                                                           (number of                                                 (%)      (%)       persons)                                        ______________________________________                                        Example 66   99.9       100       20                                          Example 67   99         99.5      19                                          Example 68   95         97        18                                          Example 69   90         93        15                                          Example 70   85         90        13                                          Comparative Example 40                                                                     80         86         7                                          Comparative Example 41                                                                     70         78         0                                          Comparative Example 42                                                                     57         66         0                                          ______________________________________                                    

Examples 71 to 75 and Comparative Examples 43 to 45

Cleansing creams were prepared by using isopropyl oleates which areoleic acid derivatives having different purities shown in Table 15 asthe oily substance and polyoxyethylated (20 mols) oleyl ethers andpolyoxyethylated (5 mols) sorbitan monooleates which are oleic acidderivatives having the same purities as those of the correspondingisopropyl oleates, respectively, as the surfactants according to theformulation described below and the feeling in use was evaluated. Theresults are shown in Table 15.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance:                                                                           isopropyl oleate    80%                                           surfactants:                                                                              polyoxyethylated (20 mols)                                                                         3%                                                       oleyl ether                                                                   polyoxyethylated (5 mols)                                                                          2%                                                       sorbitan monooleate                                               watery component                                                                          purified water      15%                                           ______________________________________                                    

                  TABLE 15                                                        ______________________________________                                                   purity of cis-                                                                         purity of cis-                                                                          evaluation of                                              Δ9-octa-                                                                         Δ9- feeling in use                                             decenoic acid                                                                          alkenoic acid                                                                           (number of                                                 (%)      (%)       persons)                                        ______________________________________                                        Example 71   99.9       100       20                                          Example 72   99         99.5      20                                          Example 73   95         97        18                                          Example 74   90         93        18                                          Example 75   85         90        13                                          Comparative Example 43                                                                     80         86         7                                          Comparative Example 44                                                                     70         78         0                                          Comparative Example 45                                                                     57         66         0                                          ______________________________________                                    

Examples 76 to 80 and Comparative Examples 46 to 48

Cleansing foams were prepared by using oleyl alcohols which are oleicacid derivatives having different purities shown in Table 16 as the oilysubstance and potassium oleates which are oleic acid derivatives havingthe same purities as those of the corresponding oleyl alcohols as thesurfactant according to the formulation described below and the feelingin use was evaluated. The results are shown in Table 16.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance:                                                                           oleyl alcohol        3%                                           surfactant: potassium oleate    40%                                           watery component                                                                          purified water      57%                                           ______________________________________                                    

                  TABLE 16                                                        ______________________________________                                                   purity of cis-                                                                         purity of cis-                                                                          evaluation of                                              Δ9-octa-                                                                         Δ9- feeling in use                                             decenoic acid                                                                          alkenoic acid                                                                           (number of                                                 (%)      (%)       persons)                                        ______________________________________                                        Example 76     99.9     100       20                                          Example 77   99           99.5    19                                          Example 78   95         97        18                                          Example 79   90         93        18                                          Example 80   85         90        14                                          Comparative Example 46                                                                     80         86         9                                          Comparative Example 47                                                                     70         78         0                                          Comparative Example 48                                                                     57         66         0                                          ______________________________________                                    

Examples 81 to 85 and Comparative Examples 49 to 51

Cleansing foams were prepared by using ethylene glycol monooleates whichare oleic acid derivatives having different purities shown in Table 17as the oily substance and monosodium N-oleoylglutamates which are oleicacid derivatives having the same purities as those of the correspondingethylene glycol monooleates as the surfactant according to theformulation described below and the feeling in use was evaluated. Theresults are shown in Table 17.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance:                                                                           ethylene glycol monooleate                                                                       5%                                             surfactant: monosodium N-oleoylglutamate                                                                    40%                                             watery components                                                                         purified water    50%                                                         polyethylene glycol                                                                              5%                                             ______________________________________                                    

                  TABLE 17                                                        ______________________________________                                                   purity of cis-                                                                         purity of cis-                                                                          evaluation of                                              Δ9-octa-                                                                         Δ9- feeling in use                                             decenoic acid                                                                          alkenoic acid                                                                           (number of                                                 (%)      (%)       persons)                                        ______________________________________                                        Example 81     99.9     100       20                                          Example 82   99           99.5    19                                          Example 83   95         97        18                                          Example 84   90         93        18                                          Example 85   85         90        14                                          Comparative Example 49                                                                     80         86         8                                          Comparative Example 50                                                                     70         78         7                                          Comparative Example 51                                                                     57         66         0                                          ______________________________________                                    

Examples 86 to 90 and Comparative Examples 52 to 54

Foundations of milk lotion were prepared by using isooctadecanyl oleateswhich are oleic acid derivatives having different purities shown inTable 18 as the oily substance and triethanolamine oleates which areoleic acid derivatives having the same purities as those of thecorresponding isooctadecanyl oleates as the surfactant according to theformulation described below and the feeling in use was evaluated. Theresults are shown in Table 18.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance: isooctadecanyl oleate                                                              18%                                                      surfactant: triethanolamine oleate                                                                 5%                                                       watery component                                                              purifled water       64.9%                                                    pigments                                                                      titanium dioxide     8%                                                       talc                 4%                                                       color                0.1%                                                     ______________________________________                                    

                  TABLE 18                                                        ______________________________________                                                   purity of                                                                              purity of evaluation of                                              cis-Δ9-                                                                          cis-Δ9-                                                                           feeling in use                                             octadecenoic                                                                           alkenoic  (number of                                                 acid (%) acid (%)  persons)                                        ______________________________________                                        Example 86   99.9       100       20                                          Example 87   99         99.5      20                                          Example 88   95         97        18                                          Example 89   90         93        18                                          Example 90   85         90        18                                          Comparative Example 52                                                                     80         86        13                                          Comparative Example 53                                                                     70         78        8                                           Comparative Example 54                                                                     57         66        0                                           ______________________________________                                    

Examples 91 to 95 and Comparative Examples 55 to 57

Lipsticks were prepared by using docosenyl oleates and octacosanyloleates which are oleic acid derivatives having different purities shownin Table 19, respectively, as the oily substances and glycerolmonooleates which are oleic acid derivatives having the same purifies asthose of the corresponding docosenyl oleates and octacosanyl oleates asthe surfactant according to the formulation described below and thefeeling in use was evaluated. The results are shown in Table 19.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substances: docosenyl oleate                                                                   42%                                                     octacosanyl oleate    15%                                                     surfactant: glycerol monooleate                                                                     30%                                                     watery component                                                              glycerol               3%                                                     pigments                                                                      titanium dioxide       1%                                                     red pigment No. 201    1%                                                     red pigment No. 202    1%                                                     blue pigment No. 1 auminum chelate                                                                  0.5%                                                    mica titanium         6.5%                                                    ______________________________________                                    

                  TABLE 19                                                        ______________________________________                                                   purity of                                                                              purity of evaluation of                                              cis-Δ9-                                                                          cis-Δ9-                                                                           feeling in use                                             octadecenoic                                                                           alkenoic  (number of                                                 acid (%) acid (%)  persons)                                        ______________________________________                                        Example 91   99.9       100       20                                          Example 92   99         99.5      19                                          Example 93   95         97        18                                          Example 94   90         93        18                                          Example 95   85         90        14                                          Comparative Example 55                                                                     80         86        9                                           Comparative Example 56                                                                     70         78        7                                           Comparative Example 57                                                                     57         66        0                                           ______________________________________                                    

Examples 96 to 100 and Comparative Examples 58 to 60

Hair creams were prepared by using octadecyl oleates which are oleicacid derivatives having different purities shown in Table 20 as the oilysubstance and polyoxyethylene (10 mols) glycol monooleates which areoleic acid derivatives having the same purities as those of thecorresponding octadecyl oleates as the surfactant according to theformulation described below and the feeling in use was evaluated. Theresults are shown in Table 20.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance: octadecyl oleate                                                                      15%                                                   surfactant: polyoxylethylene (10 mols) glycol                                                          5%                                                   monooleate                                                                    watery components                                                             purified water          75%                                                   propylene glycol         5%                                                   ______________________________________                                    

                  TABLE 20                                                        ______________________________________                                                   purity of                                                                              purity of evaluation of                                              cis-Δ9-                                                                          cis-Δ9-                                                                           feeling in use                                             octadecenoic                                                                           alkenoic  (number of                                                 acid (%) acid (%)  persons)                                        ______________________________________                                        Example 96   99.9       100       20                                          Example 97   99         99.5      19                                          Example 98   95         97        18                                          Example 99   90         93        18                                          Example 100  85         90        13                                          Comparative Example 58                                                                     80         86        8                                           Comparative Example 59                                                                     70         78        0                                           Comparative Example 60                                                                     57         66        0                                           ______________________________________                                    

Examples 101 to 105 and Comparative Examples 61 to 63

Hair growth agents were prepared by using ethyl oleates which are oleicacid derivatives having different purifies shown in Table 21 as the oilysubstance and glycerol monooleates which are oleic acid derivativeshaving the same purifies as those of the corresponding ethyl oleates asthe surfactant according to the formulation described below and thefeeling in use was evaluated. The results are shown in Table 21.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance: ethyl oleate                                                                        3%                                                      surfactant: glycerol monooleate                                                                     2%                                                      watery component                                                              ethanol             93.4%                                                     hair growth components                                                        cepharanthin          1%                                                      hinokitiol          0.1%                                                      tocopherol nicotinate                                                                             0.5%                                                      ______________________________________                                    

                  TABLE 21                                                        ______________________________________                                                   purity of                                                                              purity of evaluation of                                              cis-Δ9-                                                                          cis-Δ9-                                                                           feeling in use                                             octadecenoic                                                                           alkenoic  (number of                                                 acid (%) acid (%)  persons)                                        ______________________________________                                        Example 101  99.9       100       20                                          Example 102  99         99.5      20                                          Example 103  95         97        19                                          Example 104  90         93        18                                          Example 105  85         90        14                                          Comparative Example 61                                                                     80         86        7                                           Comparative Example 62                                                                     70         78        1                                           Comparative Example 63                                                                     57         66        0                                           ______________________________________                                    

Examples 106 to 110 and Comparative Examples 64 to 66

Hair growth agents were prepared by using palmityl oleates which areoleic acid derivatives having different purities shown in Table 22 asthe oily substance and polyoxyethylene (10 mols) oleyl ether phosphoricacid sodium salts which are oleic acid derivatives having the samepurities as those of the corresponding palmityl oleates as thesurfactants according to the formulation described below and the feelingin use was evaluated. The results are shown in Table 22.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance: palmityl oleate                                                                          2%                                                 surfactants: polyoxyethylene (10 mols) oleyl ether                                                       2%                                                 phosphoric acid sodium salt                                                   watery components                                                             ethanol                   70%                                                 purified water           24.4%                                                hair growth components                                                        capronium chloride         1%                                                 extract of Japanese green gentian                                                                      0.1%                                                 α-tocopherol       0.5%                                                 ______________________________________                                    

                  TABLE 22                                                        ______________________________________                                                   purity of                                                                              purity of evaluation of                                              cis-Δ9-                                                                          cis-Δ9-                                                                           feeling in use                                             octadecenoic                                                                           alkenoic  (number of                                                 acid (%) acid (%)  persons)                                        ______________________________________                                        Example 106  99.9       100       20                                          Example 107  99         99.5      19                                          Example 108  95         97        18                                          Example 109  90         93        18                                          Example 110  85         90        13                                          Comparative Example 64                                                                     80         86        9                                           Comparative Example 65                                                                     70         78        0                                           Comparative Example 66                                                                     57         66        0                                           ______________________________________                                    

Examples 111 to 115 and Comparative Examples 67 to 69

Emulsion compositions were prepared by using glycerol trioleates whichare oleic acid derivatives having different purities shown in Table 23as the oily substance and sorbitan sesquioleates and polyoxyethylene (20mols) sorbitan monooleates which are oleic acid derivatives having thesame purities as those of the corresponding glycerol trioleates,respectively, as the surfactants according to the formulation describedbelow.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance: glycerol trioleate                                                                  50%                                                     surfactants: sorbitan sesquioleate                                                                  8.5%                                                    polyoxylethylene (20 mols) sorbitan                                                                 1.5 .sup.                                               monooleate                                                                    watery component                                                              purified water        40%                                                     ______________________________________                                    

                  TABLE 23                                                        ______________________________________                                                     purity of cis-Δ9-                                                                  purity of cis-Δ9-                                            octadecenoic acid                                                                        alkenoic acid                                                      (%)        (%)                                                   ______________________________________                                        Example 111    99.9         100                                               Example 112    99           99.5                                              Example 113    95           97                                                Example 114    90           93                                                Example 115    85           90                                                Comparative Example 67                                                                       80           86                                                Comparative Example 68                                                                       70           78                                                Comparative Example 69                                                                       57           66                                                ______________________________________                                    

Storage stability of the emulsion compositions thus prepared wasevaluated. The results on the condition of the emulsion and the storagestability on standing are shown in Table 24.

                                      TABLE 24                                    __________________________________________________________________________    condition of                                                                              storage stability on standing, after the specified time           emulsion    30 min.                                                                            1 hour                                                                             5 hours                                                                             24 hours                                                                           72 hours                                     __________________________________________________________________________    Example 111                                                                         good  stable                                                                             stable                                                                             stable                                                                              stable                                                                             stable                                       Example 112                                                                         good  stable                                                                             stable                                                                             stable                                                                              stable                                                                             stable                                       Example 113                                                                         good  stable                                                                             stable                                                                             stable                                                                              stable                                                                             stable                                       Example 114                                                                         good  stable                                                                             stable                                                                             stable                                                                              stable                                                                             stable                                       Example 115                                                                         good  stable                                                                             stable                                                                             stable                                                                              stable                                                                             slightly                                                                      separated                                    Comparative                                                                         good  stable                                                                             stable                                                                             slighly                                                                             separated                                                                          separated                                    Example 67            separated                                               Comparative                                                                         good  stable                                                                             slighly                                                                            separated                                                                           separated                                                                          separated                                    Example 68       separated                                                    Comparative                                                                         good  stable                                                                             slightly                                                                           separated                                                                           separated                                                                          separated                                    Example 69       separated                                                    __________________________________________________________________________

Comparative Examples 70 to 72

Emulsion compositions were prepared by the same method used in Examples111 to 115 and in Comparative Examples 67 to 69 except that sorbitansesquioleate and polyoxyethylene (20 mols) sorbitan monooleate as thesurfactants were replaced by 8.5% of sorbitan sesquistearate which is aderivative of 99% stearic acid and 1.5% of polyoxyethylene (20 mols)sorbitan monostearate as the surfactants in Comparative Example 70, by10% of polyoxyethylene (2 mols) nonylphenyl ether as the surfactant inComparative Example 71 and by 10% of glycerol monolaurate which is aderivative of 99% lauric acid as the surfactant in Comparative Example72 and the storage stability of emulsion was evaluated. The results areshown in Table 25. The results show that the storage stability ofemulsion is inferior when the compounds other than the derivatives ofcis-Δ9-octadecenoic acid are used as the surfactant.

                  TABLE 25                                                        ______________________________________                                        condition    storage stability on standing,                                   of           after the specified time                                         emulsion     30 min.  1 hour   5 hours                                                                              24 hours                                ______________________________________                                        Comparative                                                                           poor     separated                                                                              separated                                                                            separated                                                                            separated                             Example 70                                                                    Comparative                                                                           poor     slightly slightly                                                                             separated                                                                            separated                             Example 71       separated                                                                              separated                                           Comparative                                                                           poor     slightly separated                                                                            separated                                                                            separated                             Example 72       separated                                                    ______________________________________                                    

Examples 116 to 120 and Comparative Examples 73 to 75

Emulsion compositions were prepared by using ethyl oleates which areoleic acid derivatives having different purities shown in Table 26 asthe oily substance and sorbitan sesquioleates and polyoxyethylene (20mols) sorbitan monooleates which are oleic acid derivatives having thesame purities as those of the corresponding ethyl oleates, respectively,as the surfactants according to the formulation described below.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance: ethyl oleate                                                                               50%                                              surfactants: sorbitan sesquioleate                                                                        7.5%                                              polyoxylethylene (20 mols) sorbitan                                                                       2.5%                                              monooleate                                                                    watery component                                                              purified water               40%                                              ______________________________________                                    

                  TABLE 26                                                        ______________________________________                                                    purity of cis-Δ9-                                                                  purity of cis-Δ9-                                            octadecenoic acid                                                                        alkenoic acid                                                      (%)        (%)                                                    ______________________________________                                        Example 116   99.9         100                                                Example 117   99           99.5                                               Example 118   95           97                                                 Example 119   90           93                                                 Example 120   85           90                                                 Comparative Example 73                                                                      80           86                                                 Comparative Example 74                                                                      70           78                                                 Comparative Example 75                                                                      57           66                                                 ______________________________________                                    

Storage stability of the emulsion compositions thus prepared wasevaluated. The results on the condition of the emulsion and the storagestability on standing are shown in Table 27.

                  TABLE 27                                                        ______________________________________                                                     storage stability on standing,                                   condition    after the specified time                                         of                                 24    72                                   emulsion     30 min. 1 hour  5 hours                                                                             hours hours                                ______________________________________                                        Example 116                                                                           good     stable  stable                                                                              stable                                                                              stable                                                                              stable                             Example 117                                                                           good     stable  stable                                                                              stable                                                                              stable                                                                              stable                             Example 118                                                                           good     stable  stable                                                                              stable                                                                              stable                                                                              stable                             Example 119                                                                           good     stable  stable                                                                              stable                                                                              stable                                                                              slightly                                                                      sep-                                                                          arated                             Example 120                                                                           good     stable  stable                                                                              stable                                                                              stable                                                                              slightly                                                                      sep-                                                                          arated                             Comparative                                                                           good     stable  stable                                                                              slightly                                                                            sep-  sep-                               Example 73                     sep-  arated                                                                              arated                                                            arated                                         Comparative                                                                           good     stable  slightly                                                                            sep-  sep-  sep-                               Example 74               sep-  arated                                                                              arated                                                                              arated                                                      arated                                               Comparative                                                                           good     stable  slightly                                                                            sep-  sep-  sep-                               Example 75               sep-  arated                                                                              arated                                                                              arated                                                      arated                                               ______________________________________                                    

Examples 121 to 125 and Comparative Examples 76 to 78

Emulsion compositions were prepared by using oleyl alcohols which areoleic acid derivatives having different purities shown in Table 28 asthe oily substance and sorbitan sesquioleates and polyoxyethylene (20mols) sorbitan monooleates which are oleic acid derivatives having thesame purities as those of the corresponding oleyl alcohols,respectively, as the surfactants according to the formulation describedbelow.

    ______________________________________                                        Formulation                                                                   ______________________________________                                        oily components                                                               oily substance: oleyl alcohol                                                                              50%                                              surfactants: sorbitan sesquioleate                                                                        8.5%                                              polyoxylethylene (20 mols) sorbitan                                                                       1.5                                               monooleate                                                                    watery component                                                              purified water               40%                                              ______________________________________                                    

                  TABLE 28                                                        ______________________________________                                                    purity of cis-Δ9-                                                                  purity of cis-Δ9-                                            octadecenoic acid                                                                        alkenoic acid                                                      (%)        (%)                                                    ______________________________________                                        Example 121   99.9         100                                                Example 122   99           99.5                                               Example 123   95           97                                                 Example 124   90           93                                                 Example 125   85           90                                                 Comparative Example 76                                                                      80           86                                                 Comparative Example 77                                                                      70           78                                                 Comparative Example 78                                                                      57           66                                                 ______________________________________                                    

Storage stability of the emulsion compositions thus prepared wasevaluated. The results on the condition of the emulsion and the storagestability on standing are shown in Table 29.

                  TABLE 29                                                        ______________________________________                                                     storage stability on standing,                                   condition    after the specified time                                         of                                 24    72                                   emulsion     30 min. 1 hour  5 hours                                                                             hours hours                                ______________________________________                                        Example 121                                                                           good     stable  stable                                                                              stable                                                                              stable                                                                              stable                             Example 122                                                                           good     stable  stable                                                                              stable                                                                              stable                                                                              stable                             Example 123                                                                           good     stable  stable                                                                              stable                                                                              stable                                                                              stable                             Example 124                                                                           good     stable  stable                                                                              stable                                                                              stable                                                                              stable                             Example 125                                                                           good     stable  stable                                                                              stable                                                                              stable                                                                              stable                             Comparative                                                                           good     stable  stable                                                                              stable                                                                              stable                                                                              sep-                               Example 76                                 arated                             Comparative                                                                           good     stable  stable                                                                              stable                                                                              sep-  sep-                               Example 77                           arated                                                                              arated                             Comparative                                                                           good     stable  stable                                                                              slightly                                                                            sep-  sep-                               Example 78                     sep-  arated                                                                              arated                                                            arated                                         ______________________________________                                    

As the results in Tables 24, 25, 27 and 29 show, the emulsioncompositions having very excellent storage stability can be prepared bythe formulations of Examples 111 to 125, which contain oleic acid oroleic acid derivatives containing cis-Δ-9-octadecenoic acid in highconcentrations as the oily substance and oleic acid derivativescontaining cis-Δ9-octadecenoic acid in high concentrations as thesurfactant.

INDUSTRIAL APPLICABILITY

As described above, the cosmetic composition of the invention is usefulas various kinds of cosmetic materials, such as skin lotion, cream, milklotion, cleansing foam and the like.

The emulsion composition of the invention can provide an emulsion havingexcellent storage stability of emulsion. This emulsion can be utilizedas a base material for pharmaceuticals, an emulsifying agent for oilymaterials which are not easily emulsified and the like as well as thecosmetic material.

We claim:
 1. An emulsion composition which comprises 0.1 to 99 weight %of a first component and 99.9 to 1 weight % of a second component whichis water soluble, the first component comprising 85 or more weight % ofa cis-Δ9-octadecenoic acid or a derivative thereof, included within 90weight % or more of a cis-Δ9-alkenoic acid or a derivative thereof,wherein the first component is either insoluble in the second component,dissolved in the second component or emulsified in the second component.2. An emulsion composition as claimed in claim 1, wherein the firstcomponent comprises a mixture of a substance insoluble in the secondcomponent and a surfactant dissolved or emulsified in the secondcomponent.
 3. An emulsion composition as claimed in claim 2, wherein thesubstance insoluble in the second component is an ester or a monohydricalcohol.
 4. An emulsion composition as claimed in claim 2, wherein theester insoluble in the second component is an ester ofcis-Δ9-octadecenoic acid and a monohydric alcohol or an ester ofcis-Δ9-octadecenoic acid and a polyhydric alcohol.
 5. An emulsioncomposition as claimed in claim 2, wherein the monohydric alcoholinsoluble in the second component is cis-Δ9-octadecenol.
 6. An emulsioncomposition as claimed in claim 2, wherein the surfactant dissolved oremulsified in the second component is an ester of cis-Δ9-octadecenoicacid and a polyhydric alcohol or an ester of cis-Δ9-octadecenoic acidand a polyoxyethylated polyhydric alcohol.
 7. An emulsion composition asclaimed in claim 1, wherein the second component is water, an alcohol, asugar, a mucopolysaccharide, an amino acid or a protein.
 8. The emulsioncomposition of claim 1, wherein the first component contains fatty acidsother than cis-Δ9-alkenoic acid, or derivatives of fatty acids otherthan cis-Δ9-alkenoic acids or mixtures thereof.
 9. The emulsioncomposition of claim 1, wherein the first component comprisesderivatives of the cis-Δ9-alkenoic acids, including cis-Δ9-octadecenoicacid, are salts of the acids, amides of the acids, esters of the acids,cis-Δ9-alkenols, ethers of cis-Δ9-alkenols, esters of cis-Δ9-alkenols,cis-Δ9-alkenylamines, salts of cis-Δ9-alkenylamines with an acid orquaternary ammonium salts of cis-Δ9-alkenylamines.
 10. The emulsioncomposition of claim 1, wherein the first component comprisesderivatives of the cis-Δ9-alkenoic acids, including cis-Δ9-octadecenoicacid, selected from the group consisting of: salts of the acids withalkali metals, alkylamines, alkanolamines or basic amino acids; ammoniumsalts of the acids; morpholine salts of the acids; amides of the acidswith alkylamines, alkenylamines, alkanolamines, amino acids orN-methyltaurine; polyoxyethylated or polyoxypropylated compounds ofamides of the acids with alkylamines, alkenylamines or alkanolamines;cis-Δ9-alkenoyl peptides; esters of the acids with monohydric alcoholsor polyoxyethylated or polyoxypropylated compounds of monohydricalcohols; esters of the acids with polyhydric alcohols orpolyoxyethylated or polyoxypropylated compounds of polyhydric alcohols;esters of the acids with sugar compounds; esters and salts of the acidswith sterols; esters of the acids with tocopherol, oryzanol, guaiacol,gossypol, terpene alcohols, fluoroalcohols, or isethionic acid;phospholipids wherein the acyl group of a cis-Δ9-alkenoic acid isintroduced; cis-Δ9-alkenols and polyoxyethylated or polyoxypropylatedcompounds thereof; phosphoric esters, sulfuric esters, polyoxyethylatedphosphoric esters, polyoxyethylated sulfuric esters, polyoxypropylatedphosphoric esters, or polyoxypropylated sulfuric esters ofcis-Δ9-alkenols and salts thereof; esters, partial esters or partialester salts of cis-Δ9-alkenyl alcohols with carboxylic acids orhydroxylated carboxylic acids; ethers of cis-Δ9-alkenols with alcohols,or sugars of other hydroxyl compounds; salts of cis-Δ9-alkenylamineswith acids; quaternary ammonium salts having a cis-Δ9-alkenyl group;and, quaternary ammonium betaine having a cis-Δ9-alkenyl group.
 11. Theemulsion composition of claim 1, wherein the first component comprisesderivatives of the cis-Δ9-alkenoic acids, including cis-Δ9-octadecenoicacid, selected from the group consisting of: esters ofcis-Δ9-octadecenoic acid with ethanol, isopropanol, cis-Δ9-hexadecanol,cis-Δ9-octadecanol, isooctadecanol, cholesterol and tocopherol; glyceroltri-cis-Δ9-octadecenoate; and, cis-Δ9-octadecenol.
 12. The emulsioncomposition of claim 1, wherein the first component contains: fattyacids other than cis-Δ9-alkenoic acid; derivatives of fatty acids otherthan cis-Δ9-alkenoic acids; paraffin; kerosene; squalene; plant oils;animal oils; lanoline; haze wax; hexadecanol; isooctadecanol; siliconeoils; fluorohydrocarbons; polyoxypropylated ethers; cholesterol;tocopherol; dodecandiethanolamide; or a polyoxyethylated alkylphenylether.